Charlestown Vacations from $379

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Your Charlestown Vacation

From its rich history to its coastal scenery and beyond, there's loads to love about Charlestown. Discover the wonders of this fascinating city with a Charlestown vacation package that's tailor-made for you. If visiting the sights is a must during your trip to Charlestown, make sure you stop by well-known attractions like Charlestown State Park and Charlestown Family Activities Park. Expedia is here to help you escape your daily routine. Tailor your vacation to Charlestown to suit your travel style, whatever that may be.

The Latest Charlestown vacation packages

Price found within the past 48 hours. Click for updated prices.
Caesars Southern Indiana

Caesars Southern Indiana

3.5 out of 5
Save 100% on your flight
Price was $588, price is now $379 per person
$379
per person
Sep 25 - Sep 29
found 7 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Louisville (SDF)
8.2/10 Very Good! (1,007 reviews)
Cockroaches in the hotel room bathroom. Dumpy, dirty and outdated rooms.

Reviewed on Aug 18, 2025

Louisville Marriott Downtown

Louisville Marriott Downtown

4 out of 5
Downtown Louisville
Save 100% on your flight
Price was $674, price is now $487 per person
$487
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Louisville (SDF)
9/10 Wonderful! (1,002 reviews)
Closed drapes, but couldn't open in morning. I got a handicap room, didn't request it but i assume check in person saw i had a walking stick and gave me one. Great. It was at the end of hall, as far away from elevators as possible. Why would you put handicap room there.

Reviewed on Aug 12, 2025

Hyatt House Louisville East

Hyatt House Louisville East

2 out of 5
Price was $636, price is now $465 per person
$465
per person
Nov 6 - Nov 11
found 23 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Louisville (SDF)
9.6/10 Exceptional! (1,003 reviews)
The rooms are very clean. The staff is amazing.

Reviewed on Aug 19, 2025

Derby City Gaming & Hotel - A Churchill Downs Property

Derby City Gaming & Hotel - A Churchill Downs Property

4 out of 5
Price was $569, price is now $421 per person
$421
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Louisville (SDF)
9.4/10 Exceptional! (1,383 reviews)
Property was super clean, nice, the hotel rooms were quiet, however the hot water took way too long to actually turn hot and the front desk was less than friendly

Reviewed on Aug 22, 2025

Embassy Suites Louisville Downtown

Embassy Suites Louisville Downtown

4 out of 5
Downtown Louisville
Save 100% on your flight
Price was $522, price is now $395 per person
$395
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Louisville (SDF)
9/10 Wonderful! (1,007 reviews)
Very nice clean hotel and wonderful breakfast. I would definitely stay there again

Reviewed on Aug 19, 2025

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Discover the most popular places to visit in Charlestown

Charlestown Family Activities Park

Enjoy a fun-filled day at Charlestown Family Activities Park during your trip to Charlestown. Stroll along the riverfront or discover the area's sunrises.

Charlestown Family Activities Park

Charlestown Hotel Deals

Galt House Hotel Trademark Collection by Wyndham

Galt House Hotel Trademark Collection by Wyndham

4 out of 5
140 North Fourth Street, Louisville, KY
Fully refundableReserve now, pay when you stay
$122 nightly
The price is $144 total per night from Sep 2 to Sep 3
$144 total
Sep 2 - Sep 3
Total with taxes and fees
8.8/10 Excellent! (3,529 reviews)
First time visitor
"Great stay! Wonderful location and outdoor pool."

Reviewed on Aug 21, 2025

Galt House Hotel Trademark Collection by Wyndham
Crowne Plaza Louisville Airport Expo Ctr by IHG

Crowne Plaza Louisville Airport Expo Ctr by IHG

3.5 out of 5
830 Phillips Lane, Louisville, KY
Fully refundable
$111 nightly
The price is $131 total per night from Aug 25 to Aug 26
$131 total
Aug 25 - Aug 26
Total with taxes and fees
8.6/10 Excellent! (759 reviews)
"Very nice. Clean and pool was very nice."

Reviewed on Aug 21, 2025

Crowne Plaza Louisville Airport Expo Ctr by IHG
Omni Louisville Hotel

Omni Louisville Hotel

4 out of 5
400 S. 2nd Street, Louisville, KY
Fully refundableReserve now, pay when you stay
$185 nightly
The price is $218 total per night from Aug 29 to Aug 30
$218 total
Aug 29 - Aug 30
Total with taxes and fees
9.2/10 Wonderful! (1,559 reviews)
"Staff were friendly and supportive"

Reviewed on Aug 21, 2025

Omni Louisville Hotel
See all 1,977 properties in Charlestown
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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Frequently asked questions

How much does a Charlestown vacation package cost?
Offering excellent value package deals from $379 on Expedia, you'll be surprised at how little a vacation to Charlestown costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Charlestown?
February, July and August are great times to look for cheap Charlestown vacation packages. Opting to travel in less busy periods means you can typically find better prices on flights and hotels.
How many days is enough for Charlestown?
The ideal length for your Charlestown vacation depends on what you'd like to see and do. Typically, a handful of days to a week will give you enough time to visit all the main attractions and discover some hidden treasures along the way.
Is it worth booking a vacation package to Charlestown?
Charlestown is a good vacation destination with attractions like Charlestown State Park among the many things to keep you entertained. Whether you're traveling with the family or planning a trip with friends, a Charlestown vacation promises a good time for everyone.
How to find the best Charlestown package deals?
Bagging a cheap Charlestown package deal is a breeze with Expedia. Once you've entered your preferred dates and destination under our "Packages" tab, set your budget range, add a couple of filters and see what's available. You can personalize your search by "Amenities," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to discover the most economical Charlestown package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a Charlestown vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your flight, hotel and car rental into one great-value price and enjoy significant savings. You'll usually get a better deal than booking each component separately. And you'll still get the flexibility to create a customized Charlestown vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Charlestown?
Enjoy fantastic discounts by booking your flights in advance with Expedia. If spontaneity is more your thing, snap up one of our last-minute deals for a spur-of-the-moment Charlestown break.
Does Expedia offer Book Now, Pay Later Charlestown vacation packages?
If you're like us, you love traveling the world but are not a fan of the price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the cost of your Charlestown break over 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can secure cheap vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.